CN101656297B - 含有高分子半导体的电子装置 - Google Patents
含有高分子半导体的电子装置 Download PDFInfo
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- CN101656297B CN101656297B CN2009101617671A CN200910161767A CN101656297B CN 101656297 B CN101656297 B CN 101656297B CN 2009101617671 A CN2009101617671 A CN 2009101617671A CN 200910161767 A CN200910161767 A CN 200910161767A CN 101656297 B CN101656297 B CN 101656297B
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- alkyl
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- 229920000642 polymer Polymers 0.000 title claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000010409 thin film Substances 0.000 claims abstract description 8
- 239000004065 semiconductor Substances 0.000 claims description 58
- 238000009434 installation Methods 0.000 claims description 22
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 9
- 230000021615 conjugation Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 8
- 239000000758 substrate Substances 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229930192474 thiophene Natural products 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000002322 conducting polymer Substances 0.000 description 4
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- 238000000151 deposition Methods 0.000 description 4
- -1 oxadiazole (bioxadiazole) Chemical compound 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- 229920003026 Acene Polymers 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
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- 229910003472 fullerene Inorganic materials 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- WSYXFYIAMXEAJT-UHFFFAOYSA-N 3h-dithiadiazole Chemical compound N1SSC=N1 WSYXFYIAMXEAJT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- YIMPFANPVKETMG-UHFFFAOYSA-N barium zirconium Chemical compound [Zr].[Ba] YIMPFANPVKETMG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
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- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US12/193,189 US7928433B2 (en) | 2008-08-18 | 2008-08-18 | Electronic device comprising semiconducting polymers |
US12/193189 | 2008-08-18 |
Publications (2)
Publication Number | Publication Date |
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CN101656297A CN101656297A (zh) | 2010-02-24 |
CN101656297B true CN101656297B (zh) | 2013-09-18 |
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Application Number | Title | Priority Date | Filing Date |
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CN2009101617671A Expired - Fee Related CN101656297B (zh) | 2008-08-18 | 2009-08-14 | 含有高分子半导体的电子装置 |
Country Status (6)
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---|---|
US (1) | US7928433B2 (enrdf_load_stackoverflow) |
EP (1) | EP2157119B1 (enrdf_load_stackoverflow) |
JP (1) | JP5106489B2 (enrdf_load_stackoverflow) |
KR (1) | KR101506350B1 (enrdf_load_stackoverflow) |
CN (1) | CN101656297B (enrdf_load_stackoverflow) |
CA (1) | CA2675081C (enrdf_load_stackoverflow) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US7928181B2 (en) * | 2008-08-18 | 2011-04-19 | Xerox Corporation | Semiconducting polymers |
US8440299B2 (en) * | 2010-02-25 | 2013-05-14 | LGS Innovations LLC | Composite dielectric material for high-energy-density capacitors |
US9214258B2 (en) | 2012-12-06 | 2015-12-15 | Xerox Corporation | Semiconductor composites comprising carbon nanotubes and diketopyrrolopyrrole-thiophene based copolymers |
US9399698B2 (en) | 2014-01-31 | 2016-07-26 | Xerox Corporation | Processes for purifying diketopyrrolopyrrole copolymers |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1891732A (zh) * | 2004-07-08 | 2007-01-10 | 三星电子株式会社 | 含有低聚噻吩和n-型杂芳族单元的有机半导体共聚物 |
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US1459375A (en) * | 1922-07-24 | 1923-06-19 | Jr Christopher Blom Olsen | Safety receptacle for bottles and the like |
US3238183A (en) * | 1963-01-28 | 1966-03-01 | Du Pont | Aromatic poly-1, 3, 4-oxadiazoles and process of making same |
US3357956A (en) * | 1965-03-30 | 1967-12-12 | Du Pont | Polymeric 1, 3, 4-thiadiazoles and the process for their preparation |
US3385837A (en) * | 1965-07-15 | 1968-05-28 | Du Pont | Poly |
FR1459375A (fr) | 1965-10-20 | 1966-04-29 | Westinghouse Electric Corp | Copolymères linéaires oxadiazole-imide |
US3476719A (en) * | 1967-02-28 | 1969-11-04 | Du Pont | 1,3,4-thiadiazole-1,3,4-oxadiazole polymers |
DE19840195C1 (de) * | 1998-09-03 | 2000-06-15 | Fraunhofer Ges Forschung | Aromatische Poly(1,3,4-heterodiazole), Verfahren zu ihrer Herstellung und ihre Verwendung in optischen Vorrichtungen, insbesondere Elektrolumineszenzbauelementen |
CA2403480A1 (en) * | 2000-04-11 | 2001-10-18 | Dupont Displays, Inc. | Soluble poly(aryl-oxadiazole) conjugated polymers |
JP3892795B2 (ja) * | 2002-10-31 | 2007-03-14 | 株式会社東芝 | ポリイミド光学材料、ポリイミド前駆体溶液、および光導波路素子 |
JP4066802B2 (ja) * | 2002-12-17 | 2008-03-26 | 富士ゼロックス株式会社 | ポリエステル樹脂及びそれを用いた機能素子、有機電界発光素子、並びに有機電界発光素子の製造方法 |
US20050146263A1 (en) | 2003-09-25 | 2005-07-07 | Kelly Stephen M. | Lighting elements, devices and methods |
CN101747493B (zh) * | 2003-10-28 | 2014-07-02 | 西巴特殊化学品控股有限公司 | 二酮基吡咯并吡咯聚合物 |
JP2006241267A (ja) * | 2005-03-02 | 2006-09-14 | Seiko Epson Corp | 導電性材料用組成物、導電性材料、導電層、電子デバイスおよび電子機器 |
US7758757B2 (en) * | 2007-10-19 | 2010-07-20 | E. I. Du Pont De Nemours And Company | Method for removing hydrazine compounds |
US7928181B2 (en) * | 2008-08-18 | 2011-04-19 | Xerox Corporation | Semiconducting polymers |
-
2008
- 2008-08-18 US US12/193,189 patent/US7928433B2/en active Active
-
2009
- 2009-07-29 EP EP09166662.8A patent/EP2157119B1/en active Active
- 2009-08-11 CA CA2675081A patent/CA2675081C/en not_active Expired - Fee Related
- 2009-08-12 JP JP2009187133A patent/JP5106489B2/ja not_active Expired - Fee Related
- 2009-08-14 KR KR1020090075358A patent/KR101506350B1/ko not_active Expired - Fee Related
- 2009-08-14 CN CN2009101617671A patent/CN101656297B/zh not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1891732A (zh) * | 2004-07-08 | 2007-01-10 | 三星电子株式会社 | 含有低聚噻吩和n-型杂芳族单元的有机半导体共聚物 |
Also Published As
Publication number | Publication date |
---|---|
CN101656297A (zh) | 2010-02-24 |
US7928433B2 (en) | 2011-04-19 |
KR101506350B1 (ko) | 2015-03-26 |
CA2675081C (en) | 2018-06-12 |
EP2157119B1 (en) | 2020-03-11 |
KR20100021978A (ko) | 2010-02-26 |
US20100038631A1 (en) | 2010-02-18 |
JP5106489B2 (ja) | 2012-12-26 |
EP2157119A1 (en) | 2010-02-24 |
CA2675081A1 (en) | 2010-02-18 |
JP2010045367A (ja) | 2010-02-25 |
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